History Repeats Itself, Sort Of
by twilightobsessedfan93
Summary: Starts at the goodbye Tristan scene in Run Away Little Boy. What if history repeated itself with Rory, but things turned out a little differently for her than they did for her mother?
1. Chapter 1

Chapter 1

(Set in Run Away Little Boy right before Tristan leaves)

"I'd kiss you but your boyfriend's watching" Tristan sadly confesses.

Rory looks at him with pleading eyes and whispers gently "Goodbye Tristan, I really will miss you." "Bye Mary", Tristan hesitates before saying, "I mean Rory."

At the sound of Tristan calling her by her given name, Rory smiles slightly. The last second before his father yells for him to come, he leans in and gives Rory the hug she was hoping she would get before she said goodbye to Tristan forever. As he walks away, "Tristan wait!" Rory cried.

"Roryyyyyy… try not to make this harder than it already is." he pleads. Rory looks at him with her tear-filled eyes and sadly says, "I… I think I'm in love with you." "Well I love you too my Mary." Tristan whispers.

He takes hold of her hands and looks straight into her ocean blue eyes as he says "Well than that settles it. I'm refusing to leave. I'm almost seventeen and I should be able to make that decision myself. I don't care what I have to do, I am NOT leaving you now." Rory starts to ramble as she always does when she is flustered. "But what about the safe with Duncan and Bowman, and the police, and your parents, and military…"

At this point, Tristan cuts her off with the most wonderful, sweet, gentle kiss she has ever experienced.

Dean sees the whole exchange occur and the kiss was the last straw. He storms over to Tristan and prepares to punch him in the jaw. As he pulls back his fist to hit him, Rory tries to talk some sense into her soon-to-be ex. "Dean, I'm so sorry but I can't be with you anymore. You were the most amazing first boyfriend I could EVER wish for, and the times we've had together I will always cherish. But I won't and can't string you along any further. In case you didn't hear any of my previous conversation with Tristan, I love him, and we want to be together."

Dean sighs and looks at Rory in a way that she can tell he isn't mad. "I understand Rory. I've had a sneaking suspicion that this would happen ever since I came to Chilton the day we got back together. Even though I do believe you didn't know how you felt about him, I could tell from then on that something had changed." Rory smiled because she knew that that day was when she realized that Tristan was special to her, but she pushed that thought away for a while until she could confront Dean about it.

"I know it sounds cliché but I NEVER want to hurt you and I hope we can still be friends?" Dean grins, "I don't think I'll ever stop loving you but I'll take what I can get, even if that just means a best friend."

Dean and Rory share a hug before he walks back to Sookie, Lorelai, and Lane. Mr. DuGrey had since walked over to Tristan to try and get him out to the car. They started arguing and Tristan calmly says "Dad, I want to propose something to you."

"No! You are going to miss your plane if you continue trying to distract me with your nonsense." His father says very quietly, trying not to cause a spectacle.

"Please father? Just hear me out."

"Alright Tristan, if it will get you on that plane in a half hour, you've got 2 minutes."

"Thank you Dad, that's all I need."

" 1 minute 46 seconds."

" Okay, so I've met this girl, I know what you're thinking, but being deprived of hot girls is not my reason for refusing to go to military school. So anyway, this girl is Rory Gilmore."

At this point, his father interrupts, "You mean grand-daughter of Emily and Richard Gilmore?" "Yup, that's the one!"

"Alright, get on with your story."

"Okay so Rory has always acted like she hates me, even though I've loved her since the day I met her. We had a Shakespeare assignment to perform one act of Romeo and Juliet tonight. It was the death scene and I was playing Romeo to her Juliet. As I was saying goodbye to her before the show, she told me she finally realized that she loves me. This might be my only chance to be with her and you'll be taking that away if you send me to military school in North Carolina."

Rory starts to cry and looks at Mr. DuGrey with pleading puppy-dog eyes. His father pinches his nose in frustration and looks at the crying young girl one more time before compromising with him, "Well, I guess if you stop the criminal activity with Duncan and Bowman and stay on your toes we can work out a way for you to stay. But that does NOT mean slacking off and reverting back to your old ways. I've heard that Ms. Gilmore here is a very ambitious student and very intelligent as well. Maybe her good habits will start to rub off on you."

Both Rory and Tristan put on a grin from ear-to-ear. Tristan picks Rory up off the ground and spins her around until they both get dizzy.

Tristan explodes "Did you hear that!? I'm staying, for good!" Rory replies with, "Yes! And I've never been happier!" Still being Tristan, he can't wait to ask Rory "So, are you free Friday?", since he hadn't had a non-date Friday since he was twelve.

"Well I have the weekly dinner with the grandparents but you could always come with us if you want, and we could go out for ice cream and a movie or something after."

"That sounds great! I can't wait to meet the famous Gilmores." He confesses.

She sarcastically remarks, "Oh yeah, they're famous alright, just ask my mother."

***Next, Lorelai, Rory and Tristan go for Friday night dinner at the elder Gilmore's house and Lorelai gets flashbacks of the first dinner Chris had with her parents.***


	2. Chapter 2

A/N- Alright, I'll make this short. This is the first story I've ever posted online and it was really nice to get a few positive reviews. So thanks for those!!!!! I hope this story is at least decent. It was written a few years ago but I was afraid to post it because I thought people wouldn't like it. I will post the first few chapters A.S.A.P. but after that I'll actually have to write in between so it might be a bit longer between updates. Hope you like it!!!

Chapter 2

By Monday everyone knew Rory and Tristan were together, but they expected as much considering Madeline and Louise saw what happened at the Shakespeare night.

"You know, it's really nice having someone at your locker every morning greeting you with coffee." Rory told Tristan one day.

On Thursday, all Rory could think about was what the outcome of the dinner with her grandparents the next day would be.

Like past 4 days that week, when Rory walked to her locker on Friday she shared a good morning kiss and "Hello" with Tristan and he stared at her as she continued her daily routine.

"So I'm catching the bus with you after school to Stars' Hollow?"

"Sure, unless you just want to meet me and my mom in Hartford later tonight."  
"No! I want to spend as much time with you as possible."

The rest of the day went very fast for the two teenagers and by 3:00pm they both were sitting on a bench waiting for the bus to Stars' Hollow to arrive. It came and they boarded the bus taking a seat near the back.

"So what's the plan for this afternoon?" Tristan asked

"Well, when we get there we can drop our stuff at my house. Then we can get some coffee and Danish at Luke's, one of my favorite places in town. After that we can just hang out or I can give you a tour of the town."

"That sounds great!"

"Here's our stop… I think you'll like Stars Hollow and MOST of the people."

They got off the bus and slowly made their way to Rory's house. Rory unlocks the front door and both walk into the foyer."

"Mom, We're home!" Rory screamed

"WE?" Lorelai screamed back

Lorelai came barreling down the stairs before Rory replied saying, "Yeah! Remember? I told you yesterday that he was coming home with me."

"Oh. RIIIIIIIIIGHT. Bible-Boy. I forgot. Nice to meet you spawn of Satan." Lorelai teased

"MOM! STOP IT!"

Tristan wore a genuine smile as he said "It's a pleasure to meet you Ms. Gilmore."

"Oh stop calling me Ms. Gilmore. I feel so old. It's Lorelai."

Rory thought their conversation had gone far enough. "Okay, lets go drop our stuff in my room. Its right around the corner."

"DOOR STAYS OPEN AT ALL TIMES!" Rory heard her mother warn.

They walk into her room and he inspects it. "How much does it suck that they used Pink Moon in a Voltswagon commercial?" Rory starts to remember the beginning of her relationship with Dean. She quickly snaps out of it and asks if Tristan is ready for the most amazing coffee ever."

"Hell yes! Let's go!" Tristan replies (with obvious enthusiasm)

On their way to Luke's, Miss Patty sees the couple and stops them in their tracks. "And WHO is this?" She stares at Tristan like he's a piece of beef. "This is Tristan from Chilton."

"Well Helllllllo Tristan from Chilton!" He makes a face to Rory to show that he is VERY scared of Patty. She is able to save him from the disaster that is Miss Patty by telling the woman they have somewhere they need to be.

"She was interesting…" Tristan settled for telling Rory this, instead of what he was really thinking. That Miss Patty was nuts.

"That's my town for you, interesting."

Finally at Luke's the overhead bell rang as they walked in and Luke instinctively looked up. He waved at the two and smiled "Hey Rory!"

"Hi Luke! This is my friend… my boyf… this is Tristan from Chilton." She sheepishly admits.

"Hello sir." Tristan said

"I have been called many things in this diner. But never sir. It's Luke."

"Okay Luke!"  
Rory has a confused look on her face until she asks Luke why he seems so happy. "Well, I just found out that Jess is one of the top kids in his English class!"

Rory becomes very excited for Luke and her now friend Jess. "I knew he could do it! Especially since he loves to read so much!"

Luke admitted that he always thought the same thing but that Jess just needed some time to adjust to his new home and school.

Rory and Tristan ordered their food to-go and they left the diner.

As they were walking out, Jess comes storming in sending a death glare towards Tristan. Luke told him the two were together and he was quite obviously jealous.

"He has a thing for you Rory." Tristan knowingly tells his girlfriend.

"What?! No. He's Jess!"

"Alright sweet innocent Rory. Believe what you want to believe. But I can tell. I was him for the past year before we got together."

Walking towards Al's Pancake World trying to explain to Tristan why it is still called "Pancake" world even though Al hasn't sold pancakes for years, Babette yells for Rory.

"Hey Sugar!"

"Hi Babette!"

"Who's the hunk with the good butt?"

Tristan proceeds to blush while Rory smiles. "This is Tristan. I go to school with him."

"Ah! So he's smart…"

"Ummm yeah. Well. We have to go. It was nice talking to you!"

"You do that honey. Stay out of trouble with that hottie!"

Rory takes off with Tristan close behind before busting into laughter on the ground in the town square.

They walk to Kim's antiques since Tristan wants to meet the girl he's been hearing about since he and Rory met, Lane. They go right in the door since it was business hours and the door is always unlocked. They hear the infamous voice of Mrs. Kim

"Who there?"

"It's me Mrs. Kim. Rory"

"Oh. Hello. I'll go get Lane. You sit here. Wait. Who is this?"

"Oh. This is a friend of mine from school."

"Oh. So you not date?"

"No." Mrs. Kim walks away and Tristan confusedly looks at Rory wondering why she lied about their relationship.

Lane walks down the stairs. "Hi Rory! And you must be Tristan! Nice to meet you!"

"Well its nice to meet the famous Lane Kim. I've heard a lot about you."

Rory explains to Lane that she is giving Tristan a tour and that they don't have much time left, so they leave so Rory can show him one last very important place in Stars' Hollow.

"This is the Independence Inn that my mom runs."

"It's beautiful!"

"I know, and I love it."

They walk inside towards the concierge desk. "Tristan this is Michele. He works here."

"Nice to meet you sir" Tristan says. He extends his hand for Michele to shake it, but all he gets is a curt "Hello" from Michele, who never looked up from what he was doing before they came over to him.

"My mom must be in the kitchen with Sookie."

They enter the kitchen and are attacked by her mother's best friend.

"Hiiiii there. You must be the bible-boy Lorelai has been telling me about for the past week. Nice to meet you."

"You too!"

"Where's mom?"

Sookie points to her mother, who is flipping through a magazine while sitting on a stool in the corner.

"Hi Mom."

"Hey kids! How did the tour go?"

"It went great! Tristan saw almost everything and got to meet and be scared of some of the quirky people we call our friends. Well, its almost 5. We're going to go back to the house to get ready for tonight."

"Okay. See you guys in a little while!"

A/N- So, I had to stop this where it ended because if not this chapter would be never ending. I stopped it before I was planning on stopping it because this was the only reasonable place to cut it off between chapters. I know there isn't a whole lot of interesting plot points in this chapter, but Tristan needed to be introduced into Stars' Hollow! Please Review! I neeeeeeeeeed the feedback!


	3. Chapter 3

Chapter 3

Later that night Rory is in her room changing into her dinner attire while Tristan is changing down the hall in the bathroom.

"I'm ready Tristan!" Rory calls

"I'll be done in a few minutes!" Tristan tells her

"He spends more time in the bathroom than most teenage girls do!" Rory grumbles to herself. "I mean seriously. What in the world does he have to do? Brush the little bit of hair he has and put on clothes and some deodorant! That's all!"

By that time Tristan had finished in the bathroom and came up behind Rory. "I'm sorry. I just really want to make a good impression on your grandparents."

"It's okay. But… you've already met my grandparents, haven't you?"

"Well yeah. But that was when I was the son of someone your grandfather did business with. Now I'm his granddaughter's boyfriend. There's a difference."

"You just called yourself my boyfriend.."

"Um yeah… and?"

"I just wasn't expecting it so soon. I mean we haven't even technically been on a date and you are HARDLY the dating-one-girl-at-a-time type of guy."

"Well I was going to wait to tell you this until we had been dating for at least a little while but now seems like a good time. The only reason why I acted the way I did before we started going out was because it was all just for fun and I never really had feelings for any of them. They were just girls to keep me distracted from the fact that I was lonely. My parents have never been around for long periods of time and when they are around they aren't exactly nice to me. I have no siblings and quite honestly no REALLY good friends , just the ones that have fun going to parties and getting drunk with me. When I met you, all that changed. I thought I might have found someone who could fill that void and make me feel like I really mattered. So I really honestly don't WANT to date anyone else. You're the most important person in my life right now, and I don't think that's going to change any time soon."

"Tristan, I never knew you felt that way! I just thought I was another girl for you to sleep with. You're very important to me too."

Around halfway through Tristan's speech Lorelai snuck in through the front door and listened from around the corner.

When they were done with that conversation, she walked into the room and said "Awww that was so cute!"

Rory shrieked in embarrassment "MOM! How much of that did you hear?!"

"Um from about the point where Tristan said he was lonely?" Tristan turns tomato red and smiles sheepishly.

"What? I walk in the house and hear you two professing your love for one another and you think I'm not going to say anything? Of course I am!"

"Ugh you're so annoying sometimes!!! I can't have any privacy can I?"

"NOPE!" Lorelai starts up the stairs to get ready for dinner. On her way up she whispered in a high pitched bubbly voice just loud enough for Tristan and Rory to hear, "Oh Tristan, I love you too!" Rory let out an irritated sigh and Tristan had to stifle his laughter.

They sit on the couch and turn on the TV to watch until Lorelai is ready to go. Rory turns to Tristan and quietly says "I am so sorry for my INSANE MOTHER!" She raises her voice for the last two words, loud enough for Lorelai to hear all the way upstairs and scream back down "NO FUN!"

Tristan smiles at her and chuckles, "No. I actually think the relationship you have with your mom is cool. God knows that exchange would never happen between me and MY mom."

"Yeah it's really awesome sometimes for your mom and your best friend to be the same person, but at the same time it can get annoying when you just want her to be your mom and she's grilling you for details like a girl-friend would."

Lorelai comes racing down the stairs with a madwoman look on her face. "Alright troops. Move it, move it, move it or we'll be late and I really don't want to hear it from my mother if we are!"

They get into Lorelai's Jeep and pull out of the driveway. Lorelai takes out her favorite Metallica CD from her overhead CD case and gives it to Rory to put in the CD player. The first song starts and Tristan leans over to whisper in Rory's ear so Lorelai doesn't hear him, "Seriously? Metallica?", but Lorelai DID hear him and retorts "HEY! Don't be dissing my taste in toons!" Tristan is stunned that she was able to hear him and complements her on her impeccable hearing. "Why thank you! I take pride in my ears…" Tristan doesn't know how to reply to such a comment and settles with "Uh, you're welcome?" Rory is extremely proud that Tristan handled the first "Lorelai-comment" directed at him with such grace. Others would stare in a daze at her for whole minutes until someone changed the subject. "That's my boy! Just go along with everything she says and you'll do just fine!"

Lorelai acted offended by the comments made by her daughter, which made her seem like a mental patient that shouldn't be messed with. The rest of the drive was silent.

A few minutes later they pull into the driveway and Tristan obviously becomes uncomfortable. Lorelai notices and decides that Tristan should know the truth before he subjects himself to a torturous night with her parents.

"You do realize that once you tell them you're dating their precious Rory, you will be watched every minute of every day and won't be able to do ANYTHING without them knowing? We're talking Big Brother cameras EVERYWHERE. You won't be able to go to the bathroom or make a sandwich without Emily and Richard Gilmore knowing about it. Are you positive you still want to do this?"

"I really don't have a choice if I want to be with Rory do I?"

"Nope."

Rory tries to comfort her boyfriend, "It's not going to be that bad. My mom is being over-dramatic. As long as they like you, which they will, you will be fine."

They all get out of the car and knock on the front door of the Gilmore mansion. The maid answers the door and escorts the group into the living room where Emily and Richard are. The grandparents are both reading. Lorelai startles them "Hi mom, Hi dad!" Rory continues the greetings with "Hi grandma, and grandpa!" Tristan stays silent and stands staring at his shoes. Richard finally notices he is there and says "You're Janlen DuGrey's grandson correct? We met at Rory's party?" "Yes sir, that's me." Emily cuts in, "This may sound completely rude of me but I'm curious to know, what are you doing here?" Rory chose to answer for him. "Well Grandma, Tristan and I are dating."

Emily smiles and hugs Rory followed closely by Richard. "Really? Well that's wonderful!" "Yes, I approve!"

Emily goes right back to hostess mode "Can I get you some drinks?"

"Sure mom, I'll have a martini with a twist." Lorelai quickly says.

"I'll have a coke Grandma." Rory requests.

Last, Tristan says "I'll have a water." Emily knows that he is just being polite. "Really? We have coke, sprite, pepsi…" "Oh alright I'll have sprite."

The rest of the night went smoothly and they had the best Friday night dinner they have ever had.

As they are walking down the driveway to Lorelai's car at the end of the night Rory says, "See Tristan? They aren't THAT bad!"

Tristan laughs "Yeah, they were fine!"

Lorelai cracks up laughing.

Rory is excited for her first date night with Tristan so she brings it up. "So we're watching a movie at your house Tristan?"

"Mhmm, I live just around the corner so if your mom drops you off I'll just drive you home."

"Yeah sure that's fine with me." Lorelai replies.

She drops them off and tells Rory she must be home by 12.

Tristan and Rory walk in the house. She compliments him on the beauty and size of his house. They go into his movie theater room and pop in a great movie. Curled up under a blanket together, Rory and Tristan watch a great movie.

After it's over, they start to make out….. (A/N they go all the way.. but I'm not writing that scene)

11:30 pm

Rory looks at the clock and realizes what time it is. "Oh crap! I have to be back in a half-hour!!!!

Tristan drives her home and they talk about all kinds of things from Luke's coffee, to Chilton, to basketball.

He pulls into her driveway at 11:55. They kiss goodnight and she goes into the house.

Lorelai is watching TV and Rory doesn't know if she should tell her mother about her night or not so when Lorelai asks how it was she simply replies with "Good!"

Rory goes to her room and gets ready for bed, all the while thinking about the wonderful night she had with her boyfriend.

*Okay so that chapter was a bit more eventful than the last. Hope you liked it!*


	4. Chapter 4

Hey Readers!

I hope you all are still interested in this story. I'm sorry I've neglected it for such a long time. I do still think of it sometimes and tell myself "you need to keep writing" but alas, it never happens. I've been super busy this school year but I really am going to try to write some more of this story because I like writing it! Hopefully I still have interested readers…

-TOF93


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